Hydrochloric Acid → (2S,3S)-2-((tert-butoxycarbonyl)amino)-3-((R)-hex-5-en-2-yloxy)pentanoic acid

HRID 523178Notes

Reaction equation

HRID 523178 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C@@H:14]([O:17][C@@H:18]([CH2:20][CH2:21][CH:22]=[CH2:23])[CH3:19])[CH2:15][CH3:16])[C:10]([O:12]C)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1COCC1.[Li+].[OH-].Cl>CO>[C:1]([O:5][C:6]([NH:8][C@@H:9]([C@@H:14]([O:17][C@@H:18]([CH2:20][CH2:21][CH:22]=[CH2:23])[CH3:19])[CH2:15][CH3:16])[C:10]([OH:12])=[O:11])=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 90118054(2S,3S)-methyl 2-((tert-butoxycarbonyl)amino)-3-((R)-hex-5-en-2-yloxy)pentanoate

Product 1

HCID 90118157(2S,3S)-2-((tert-butoxycarbonyl)amino)-3-((R)-hex-5-en-2-yloxy)pentanoic acidYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a round-bottom flask equipped with a stir bar was added (2S,3S)-methyl 2-((tert-butoxycarbonyl)amino)-3-((R)-hex-5-en-2-yloxy)pentanoate (458 mg, 1.39 mmol), THF (5 mL) and MeOH (5 mL). To the stirred solution was added aq. LiOH (2.0 M, 2 mL). The mixture was stirred for 16 h, then was concentrated in vacuo to afford an aqueous solution. The solution was acidified with aq. HCl (1 M) and then transferred to a separatory funnel. The mixture was twice extracted with EtOAc. The combined organics were washed with brine; dried over MgSO4; filtered; then concentrated in vacuo to afford (2S,3S)-2-((tert-butoxycarbonyl)amino)-3-((R)-hex-5-en-2-yloxy)pentanoic acid as a white foam (438 mg, 100%).

Workup

  1. customTo a round-bottom flask equipped with a stir bar
  2. concentrationwas concentrated in vacuo
  3. customto afford an aqueous solution
  4. customtransferred to a separatory funnel
  5. extractionThe mixture was twice extracted with EtOAc
  6. washThe combined organics were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-53382597b4f846c6979d990b718d94f0
Source dataset
uspto-grants-2016_05
Patent number
US09334279B2

Reaction notes

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